Ammonium Hydroxide → HCID 44232009, compound

HRID 340274Notes

Reaction equation

HRID 340274 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5]2[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:4]=2[N:3]=1.[OH-].[NH4+]>C(O)C.[Ni]>[NH2:19][CH2:18][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][C:8]2[CH:9]=[N:10][C:11]3[C:6]([CH:7]=2)=[C:5]2[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:4]2=[N:3][C:2]=3[NH2:1])=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 58213676HCID 58213676, compound

Product 1

HCID 44232009HCID 44232009, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)benzonitrile (from the previous step) in ethanol and ammonium hydroxide (4:1, 0.2 M) stirred at room temperature was added raney nickel (10 eq). The reaction mixture was stirred under hydrogen atmosphere until the conversion was complete as shown by TLC. The reaction mixture was filtered through a short celite pad. The celite pad was washed with EtOAc. Combined organic extracts were concentrated under vacuum and the resulting crude residue was purified by chromatography (silica gel, 50-100% EtOAc in hexanes) to afford product 2-(4-(aminomethyl)phenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine. 1H NMR of the TFA salt: (methanol-d4): δ 8.81 (d, 1H), 8.79 (d, 1H), 8.38 (d, 1H), 7.51 (s, 1H), 7.44 (dd, 1H), 7.36 (dd, 4H), 4.07 (s, 2H), 3.29 (s, 2H), 3.20-3.14 (dd, 2H), 2.55 (s, 3H). LRMS [M+H]=343.2

Workup

  1. filtrationThe reaction mixture was filtered through a short celite pad
  2. washThe celite pad was washed with EtOAc
  3. concentrationCombined organic extracts were concentrated under vacuum
  4. customthe resulting crude residue was purified by chromatography (silica gel, 50-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-13064d4d6dfa444fa9644775a07b535e
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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